Diisopropylethylamine → HCID 86730252, compound

HRID 1850205Notes

Reaction equation

HRID 1850205 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([CH:13]([CH3:15])[CH3:14])[CH2:11][O:10][C:9]2=[O:16])[CH:5]=[CH:4][N:3]=1.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[C:29]([CH:31]([NH2:33])[CH3:32])[CH:28]=[N:27]2)=[CH:22][CH:21]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:33][C@@H:31]([C:29]2[CH:28]=[N:27][N:26]([C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[CH:30]=2)[CH3:32])[N:7]=1)([CH3:15])[CH3:14].[CH:13]([C@H:12]1[CH2:11][O:10][C:9](=[O:16])[N:8]1[C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:33][C@H:31]([C:29]2[CH:28]=[N:27][N:26]([C:23]3[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=3)[CH:30]=2)[CH3:32])[N:7]=1)([CH3:15])[CH3:14]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 16640666HCID 16640666, compoundHCID 86730167(S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Product 2

HCID 86730252HCID 86730252, compoundHCID 86730253HCID 86730253, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S)-3-(2-chloropyrimidin-4-yl)-4-isopropyloxazolidin-2-one (93 mg, 0.38 mmol), 1-(1-(4-methoxyphenyl)-1H-pyrazol-4-yl)ethanamine hydrochloride (514 mg, 2.03 mmol, 5.3 equiv) and iPr2NEt (0.605 mL, 3.46 mmol, 9.0 equiv) in DMSO (1.5 mL) was heated at 110° C. for 16 h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 70%) provided (S)-4-isopropyl-3-(2-((R)-1-(1-(4-methoxyphenyl)-1H-pyrazol-4-yl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one and (S)-4-isopropyl-3-(2-((S)-1-(1-(4-methoxyphenyl)-1H-pyrazol-4-yl)ethylamino)pyrimidin-4-yl)oxazolidin-2-one.

Workup

  1. washwashed with water (30 mL)
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc (3×8 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bcc9be0d7e6f47c3b992ad1c6174408f
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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